The Anti-Valentines Day Disaster!

This story was originally written for my email list “Stories From The Road” and is now getting republished here! If you want to get stories like this each month to your inbox and find out when I’m coming to a city near you, join my free email list!


I used to have a trend at the end of relationships in my early to mid 20s. After a break-up, I would get very mopey, but very focused and determined on comedy. This would usually involve taking as many gigs as possibles, working non-stop and stay out at open mics way too late. And on the drive home I’d blast My Chemical Romance or Brand New or Taking Back Sunday; what I have now deemed as my sad-boy Rock. This usually lasts a few months till I regain my self confidence and realize there are other bands in the world and some of the far sadder! 

During one of these phases in my life, I decided the right thing for me to do is to do an Anti-Valentines Day show! It had been about 5 months since my relationship with this girl had imploded. Not because we hated each other, but she realized that we were very clearly going in separate directions! So as the Sad-Boy of Comedy at the time I thought this would be the perfect catharsis for my very dramatically aching heart. 

The show was being put together by a friend of mine. He was a good producer and funny comedian so I trusted his judgement and decided to be on the bill. The bar was deep in the suburbs of Pittsburgh and had contacted my friend to put this show on. As he explained it to me, the customers asked for an Anti-Valentines Day Comedy show. And since the bar was small, they couldn’t really pay us, but they would cover our drinks that night. 

They should’ve just paid us.  

There were 5 comedians booked for the show. And we were supposed to kick off at 8pm, wrap up by 10pm and then there was a DJ dance party after the show. I was the first one to show up around 7pm. I met the owners of the place and asked them where the show was and was escorted to the back room. It was nice stage and big open room. It was clearly set up for rock concerts. 

Cool,” I said, “Is there a sound guy I should check in with to do a mic check!

Oh,” the woman replied, “We don’t have a microphone and sound guy is only coming in for the DJ at the end of the night. But you check out this board!

I was shocked at the nonchalance of her statement, as she left me alone with this very expensive sound board. At this point though, I had run a few shows in town and had invested in a mic-stand a microphone and would keep them in my trunk for exactly this occasion. So I called my friend booking the show and told him I’m setting up my mic because they didn’t have one. And as I was grabbing my stuff from my car, I was realizing that I was now going to be stuck there till the end of the night regardless of this evening would go. 

As I started to set things up, the other comics started working their way in. We talked to the bar owner and got some drinks. It was approaching 8pm and we now waited for this crowd that has asked for this show. I was going up fourth, so I had a little while to get my set in order. 

At around 8:15 we had a few people trickle in. 3 couples. They seemed excited. The dudes went straight to the bar and sat with the regulars and then kicked off a game of darts. The women got their drinks and joined in on the game of darts. We figured we’d give them a few minutes to settle in. Plus there might be more people that’ll be coming in. 

By 8:45 no-one new had come into this bar. And we were all on our second drinks. The bar owner walks up to us and ask why we haven’t started the show. We explain to her that comedy is active art form which requires an audience to be paying attention to what we’re saying so they can laugh. She just stared at us. 

My friend walked over to the people playing darts and told them they were going to kick off the show and they should come sit in the room. The 6 of them laughed and said they love comedy and were wondering why it hasn’t started. I would’ve walked up and explained to them how it was an active art form, but I had a feeling they’d all just stare at me. 

They told my friend to start the show and they’d join in on the fun. So he walked back to us and we decided to a shotgun style show. There would be no host, but the preceding comedian would introduce the next one. My friend went up and kicked things off at about 9, an hour later than it was supposed to start. He brought up the first comedian. 

Comic 1 went up and started doing some of his material. The audience weren’t really paying attention nor were they reacting. So he started yelling at them. This was not a good start. We didn’t really know what to do. How do you stop the Titanic from sinking after it’s smashed into the iceberg. Eventually after calling the audience dumb for wanting a comedy show and not understanding what comedy was, he says “Ok, so what do you want to talk about? Do you want a dirty joke or clean joke? What do you want? I’ll do it!” He ended his set by saying fuck you, and bringing up Comic 2. 

Comic 2 grabbed the microphone and sat on the stool and said “I’ll do one joke and then I’m doing any material or saying anything into this microphone till you guys come and sit in this room to watch this show!” He did his one joke, dropped the mic and sat there in silence for 15 minutes. No I don’t know if this was out of pity or discomfort, but the women sauntered into the room, giggling and sat in the front row. Comic 2 wanted the husbands in the room too. But they were too busy playing darts with the regulars at the bar. He picked up the mic, said one more joke and the comic that booked the show. 

He went up and kept the ladies attention and held them in the room. He weaved in and out his material and hitting on the 3 women in the room. It did help that he was a very attractive man. At the end of his set, the women seemed to be in good spirits. And now it was my turn. 

I tried to start my set by being casual and jumping into some of my material right away, but it was becoming evident that they were not really understanding what I was saying. The immigrant experience wasn’t something they had fathomed. So I paused and said “Do you guys know any of the things I’m talking about? Like do you guys know what India is?” They told the only Indians they knew were doctors. 

Sure, there’s a lot of Indians in the medical or IT field,” I replied. They asked what happened to me. “Oh, I didn’t care about human medicine. I don’t know, my mom never really pushed me into that stuff. Although the human body is fascinating.” 

I found out one of them was a nurse and was able to a little bit of material about my ex-girlfriend being a nurse, but they were reacting more to the casual material. I kept calling them cougars. At one point I got into a story about my recent break-up and the phone rang. So I decided I’ll talk to ‘Gina’ on the phone. Turns out she was one of the women’s sisters. I invited Gina to the show. She declined. I called a peach and handed the phone back to the woman. And then we got back to the story. 

At this moment one of the women’s husbands comes into the room. I ask if they were married to which he replied “No!” So I awkwardly hit on the woman from stage as he offered his wife to me. That’s a level of confidence I don’t think I’ll ever have in my life. He was the living embodiment of a Catskills joke! Following that there was a fourth woman that walked in looked around and left the room. So I made a joke about how she couldn’t handle the racial diversity of 2 black men and a brown man on stage and oddly got an applause break. 

One of the women kept getting uncomfortable at the mention of the Jewish faith in my set. So I wrapped my set with 2 quick jokes about religion and the 3 women got incredibly uncomfortable, which I of course pointed out and then kept going. As one of the women interrupted the last 20 seconds of my joke to announce she was going to the bathroom, I wrapped up my set as I reminded her that we were all adults with free will to go to the bathroom when we need to. 

I brought up the final comic of the night and went to the bar to get my last free drink. As the last comic was stage the crowd that was there to see a DJ came in and watch his set. It was the only moment where there was a full crowd in that room. He did a longer set and at the end, I packed up my gear, turned off the sound equipment, finished my drink and got the hell out there. 

I got into my car and thought, “Boy I could’ve done anything else right now. I could’ve gone to a bar by myself and got rejected the whole night, and I’m fairly certain it would’ve been better than this!” I turned up the My Chemical Romance and as the saddest of all the boys that night, drove off into the moonlight.